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Anna Maria Island Cottages

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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    37 Matching Rentals in Anna Maria IslandView all 750 rentals
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    The Tree House1 / 22
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Palm Cottage ~ This beautiful condo is just steps from the Beach!1 / 28
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    AMI Coastal Retreats- Beach Dreams 'Dream Away'1 / 31
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Songbird Cottage1 / 23
    (23)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Grill
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    • Air Conditioning
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2018
    If you are looking for a spacey and well equipped two bedroom location close to the beach for an affordable rate you have just found it!Songbird cottage is just ten minutes away...
    Reviewed 25 March 2018
    This rental is as advertised - nothing fancy, but comfortable and cozy. It reminded us of the old style lake cottages we've visited in Northern Wisconsin. It's furnished with...
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    About this property
    Songbird Cottage We live here part time and Songbird is loved. Of course, there are things that could be more high-end or updated, or there are units closer to the beach. But everything is clean and functional. And I'm pretty confident that you can't beat it at this price range. I take a...
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    Anna Maria Island, Florida 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Brand New Renovation Sea Waves Cottage1 / 16
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2018
    My wife and I stayed at this nice, updated rental and really enjoyed our time. The location was great, with a deck right on a canal. We were walking distance to the beach.The...
    Reviewed 23 March 2018
    The beach house was awesome!!! Had everything we needed. It was true to the pictures on line. Jenny the owner was awesome, got back to we when I had questions right away. We...
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    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anthony Beach Cottages Bare Feet Retreat1 / 31
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Outdoor Dining Area
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2016
    April was helpful and prompt. She made the whole process from booking to check out easy! The house was cozy and just what we were looking for. I would definitely book again
    Reviewed 27 July 2015
    I will be going back! From reservations to communication, from check in to location and the property itself, this place is magnificent!
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    About this property
    This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fireplace, and picket fencing,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    On the Beach Paradise d1 / 13
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    Steps to the beach with lots of beach seating. A great outside dining area complete with grill. Our only problem was finding a comfortable bed. Some people like the foam...
    Reviewed 20 July 2017
    The most wonderful place! we rented this place for 10 days, my daughter, grandson and myself. I fall in love with the place is perfect, nice and very clean.Location is perfect...
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    About this property
    This cottage is located 'on the beach' 3007 Avenue F, beautiful Holmes beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space for a pull-out. This quaint cottage is hidden away on a dead end street, away from it all yet close...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This STAND ALONE, VERY CHARMING, cottage is in a very peaceful setting with huge brick courtyard. This is not like most other vacation rentals that require you to climb 1-2 stories. This is a stand alone ground level home! We have just invested in a new kitchen, bathroom, lanai, living area and...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Little Mermaid On Beautiful Anna Maria Island!1 / 17
    (24)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2016
    Can't speak too highly about the Little Mermaid and Anna Maria Island. What you see is what you get. Every possible utensil and beach toy is to hand and all spotlessly clean...
    Reviewed 5 October 2016
    Wonderful place to stay. Very clean. Hope to be a repeat guest. Pet friendly. Very close to the beach.
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    About this property
    You will enjoy this adorable newly renovated vacation cottage – THE LITTLE MERMAID -- on Anna Maria Island just across the street from the Gulf of Mexico and minutes from shopping and attractions on Bradenton Beach’s popular Bridge Street! Your three parking spaces are right at the front door!!...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    AMI Coastal Retreats- Cracker Cottage Fish Tales1 / 132
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Ocean Views
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2018
    We absolutely loved staying at Fish Tales! It’s location was ideal for the beach and eating at Gulf Drive Cafe! Food was great and eating on beach was a plus also!Fish Tales was...
    Reviewed 28 December 2015
    We spent Christmas week on Bradenton Beach in this comfortable rental. There was plenty of room and it was comfortable. Everything we needed was close by and the beach was...
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    About this property
    The CRACKER COTTAGES are two individual cottages. Rent one or both: SEA STORY (733597) AND FISH TALES (739543). IF THE DATES YOU ARE LOOKING FOR ARE BOOKED ON SEA STORY, CHECK OUT THE OTHER SIDE 'FISH TALES', #739543. Each side sleeps four guests. If you need to rent a larger home please look at...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Anna Maria The Pink Flamingo1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Grill
    • DVD Player
    • Balcony
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2017
    The photos are accurate. But, in person the home is stunning. When my husband and I walked in, the first thing I said was "they must have did a background check on...
    Reviewed 1 December 2014
    LOVED, LOVED, LOVED this property! It's perfectly located right in the heart of Anna Marie island - easy in and out parking RIGHT in front of the villa. The villa was roomy for...
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    About this property
    ANNA MARIA ISLAND #3 TOP 10 ISLAND'S IN U.S.A. Palm Isle 3203,our 2 bedroom island decorated condo is across the street from the beaches of Anna Maria Island. Steps from the heated pool and fully landscaped setting, along with all the amenities of home, your family will enjoy our beach get...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Breeze cottage is located at north end of Anna Maria island. Brand new renovation, 2 bedrooms with 2 bath rooms, with private dock, sailboat direct to Bimini bay, unobstructed , natural view of Bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the last property on COQUINA BEACH, GULFSIDE, after historic Bridge Street, before the new pier. This means the pier on Coquina Beach could literally be YOUR backyard for a night, a week or even Spring Break. It doesn't get any better than this. We are booking now for our Grand Opening in...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    AMI Coastal Retreats- Cracker Cottage 'Sea Story'1 / 36
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2016
    We loved the cottage and its location. Every morning we would walk the beach and have breakfast in the Gulf Drive Cafe'. In the evening we would return to the beach for a stroll...
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    About this property
    CRACKER COTTAGES CONSISTS OF 2 SEPARATE COTTAGES IN ONE BUILDING...SEA STORY (733597) AND FISH TALES (739543). IF THE DATES YOU ARE LOOKING FOR ARE BOOKED ON SEA STORY, CHECK OUT THE OTHER SIDE 'FISH TALES' #739543. If you are looking to book a property that has at least 4 bedrooms, you would...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!1 / 49
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Porch
    • Washer
    • DVD Player
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2018
    It is shabby chic deco and close to everything. Dead end street and friendly atmosphere. 100' across street to Gulf of Mexico. A great walk path. Restaurants within walking...
    Reviewed 3 February 2018
    Fabulous location close to bridge street. Well equipped and comfortable bed. Lots of space and easy parking. Steps from the beach and also able to fish off the deck at end of...
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    About this property
    This is a beautifully renovated 2 UNIT 'Old Florida' style cottage......Great Views of the Beach & BAY..... JUST 100 FEET to the most stunning, sugar-sand beaches on the Gulf. 1 BR Beachside Unit sleeps 2-4.......2BR Bayside Unit sleeps 2-6. The rates shown are for the 1 BR unit. 2 BR unit is...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!1 / 42
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We spend 1 week in the lower apartment and it is a nearly perfect place to stay. The interior is very nice and the garden with a wonderful view is great. The bed is comfortable...
    Reviewed 27 February 2018
    We spent 2 weeks in the Green cottage. it was exceptionally clean, open, airy and right on the water with a great shared dock. The neighbors were all wonderful people.We had...
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    About this property
    We have some openings available April 8-15! Our family has lovingly restored this HISTORIC 1939 FISHING CAMP located on beautiful Sarasota Bay. You'll be surrounded by water living on the narrowest point of Anna Maria Island. Sugar sand BEACH only a 1 minute stroll away! Located at 115 South...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 15
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    the Location is Amazing, the beach is on the doorstep, this is a great Family-Friendly cottage close to everything, and very Clean! i recommend it to everyone! We'll visit again!
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    About this property
    *This is cottage # 2. PLAYA ESMERALDA has several charming units. If your dates are not available, please keep looking on the site for more PLAYA ESMERALDA cottages available. PLAYA ESMERALDA on beautiful Anna Maria Island is a charming inn 20 steps to the beach. This unit is nicely...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *This is unit COTTAGE # 1 at the charming PLAYA ESMERALDA . If this unit is not available for your dates, please keep looking in the site for other cottage available from Playa Esmeralda. PLAYA ESMERALDA on beautiful Anna Maria Island is a charming unit 20 steps to the beach. This one-bedroom...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Central Heating
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * LOCATION LOCATION LOCATION STEPS FROM THE WHITE SAND BEACH!! *This is Cottage #3 . PLAYA ESMERALDA has several charming units. Chances are a unit is available for your dates. If this unit is not available, please go on the homepage and keep looking for more PLAYA ESMERALDA cottage that may be...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    *This site is unit # 4 at the charming PLAYA ESMERALDA. If this unit is not available for your dates, please Try to find other units for PLAYA ESMERALDA units that may be available. PLAYA ESMERALDA on beautiful Anna Maria Island is a charming cottages 20 steps to the beach. This unit is...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bean Point Beach Cottage1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Internet Access
    • Cable/satellite TV
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    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2016
    This was our first visit to AMI. My booking of Bean Point Cottage was solely based on the pictures online, as it did not have any reviews. Bean Point Cottage was the perfect...
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    About this property
    Look no further for the perfect vacation rental! This three bedroom vacation rental is located on the serene north end of Anna Maria Island. Tastefully decorated with beautiful beach décor, and boasting a wonderfully open living and dining space, this vacation rental creates an exceptionally...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
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    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful brand new pool and tropical outdoor area await you in the newest of our vacation rentals, A Mermaid''s Lair! Located on the quiet north end of Anna Maria right across the street from Tampa Bay, this tastefully designed island décor house is waiting for you to settle in, relax, and...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Whispering Pines: 2BR Classic Cottage Near Beach1 / 48
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Patio
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    We stayed over Christmas a the Whispering Pines Cottage. It was well appointed and had beachy decorations which is perfect for the location. The beds were comfortable and the...
    Reviewed 1 March 2016
    Loved this Beautiful Cottage!Steps from the White Sand and Peaceful Beach.I will be back to this Sweet Island!!
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    About this property
    This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage1 / 21
    (14)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Parking
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2017
    Pineapple Cottage is located on Pine close to shops and near the beach. I loved to stay at this very clean and well maintained cottage. It has everything what's needed and is...
    Reviewed 19 May 2017
    We stayed at the Pineapple Cottage from May 11 to May 18.Just my husband and I. We loved the location. You can walk to the beach either on the gulf or the bay. Walked to Beach...
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    About this property
    Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower,professional linen service and...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wave Crest: 3BR Gulf-Front Beachfront Cottage1 / 25
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Grill
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    We stayed here at the end of June 2107. We have stayed in the same area on Anna Maria a few house to the north and love this area. It is quiet even when it's busy! Wave Crest...
    Reviewed 23 May 2016
    We were excited about renting Wave Crest due to the pictures and information we had previously received. However, nothing prepared us for this beautiful cottage with the...
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    About this property
    Take just four steps from Wave Crest's back door and sink your toes into the white sand beach of Anna Maria Island or enjoy views of the Gulf of Mexico from the deck, Florida room, or the four Adirondack chairs right on the sand. This gulf-front cottage is located directly on the beach and will...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *This site is unit # 4A. PLAYA ESMERALDA has several charming .this is a Small Studio with a bedroom and bathroom not full kitchen but refrigerator, microwave and coffee machine is offered. If your dates are not available, please Keep looking in the sites for other units at PLAYA ESMERALDA that...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *This Is COTTAGE i # 5. PLAYA ESMERALDA has several charming units, it is a small studio with just a bed, small bathroom and a kitchen. If your dates are not available, please keep looking on the site for other units at PLAYA ESMERALDA that may be available. PLAYA ESMERALDA on beautiful...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Smoking allowed
    About this property
    Lovely 2 bedroom, 1.5 bath Bay front home with boat/fishing dock. Beautiful views of the Bay. Located on a quiet street just one block to the beach. Located on Ana Maria Island.
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Salt Box Cottage is newly renovated, bright, clean, cozy and the perfect place for an Anna Maria Island vacation. This quaint vacation rental cottage is just steps to Tampa Bay and five blocks to the beautiful powder-soft, white sand beach and turquoise water of the Gulf of Mexico! Accommodations...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Crows Nest Spinnakers Cottages: 1BR Unique Rental1 / 23
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
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    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2016
    We thought almost everything about our stay at Spinnakers was good. The location was fantastic. The grounds, the amenities (awesome pool area), and the cleanliness of the place...
    Reviewed 29 January 2016
    We loved 202 56th St. (Spinnakers Cottages). We stayed in the Crows Nest. The location was perfect as it was really close to the beach and easy to take the Trolley or Monkey...
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    About this property
    Part of the Spinnakers Vacation Cottages, Crows Nest is what some have called an adult version of a tree house, so you know kids will love it! A one bedroom, one bath vacation rental that sleeps six, Crows Nest features an awesome private deck where you'll have a great space to enjoy coffee, tea...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Cabin 1 Spinnakers Cottages: Perfect for a Couple1 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
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    • Internet Access
    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2017
    I spent a great deal of time on the Internet pouring over property after property, hoping to find the perfect setup for an 20th Anniversary AMI trip. My wife and I work hard...
    Reviewed 27 April 2017
    We loved spinnakers! It was such a nice cottage! It was clean and decorated with a beachy theme.The pool was amazing!We already booked it for next yr.
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    About this property
    Part of the Spinnakers Vacation Cottages Cabin 1 is a one bedroom, one bath cottage nestled in a lush tropical landscape. Great for an anniversary celebration, honeymoon or just a getaway! Want to bring the kids? No problem, they will love it here as well! Cabin 1 sits beside the pool area, so...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom 1 Bath Cottage On The Beach This cottage is located 'on the beach' 3007 Avenue F on beautiful Holmes beach. It is the upstairs unit (2 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space. This quaint cottage is hidden away on a dead end street, away from...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cabin 2 Spinnakers Cottages: Perfect for a Couple1 / 24
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Patio
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2016
    This was our third stay in a Coastal Cottages rental and we couldn't be happier. Spinnakers cabin #2 was very cozy, like a home away from home. It had all of the amenities for...
    Reviewed 8 March 2016
    Cabin 2 at Spinnakers was clean and well maintained. The location was perfect; close to the beach and close to the dog park. It was great to have beach chairs, umbrellas...
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    About this property
    Part of the Spinnakers Vacation Cottages Cabin 2 is a one bedroom, one bath cottage nestled in a lush tropical landscape. Surrounded by palms, plumeria, jasmine and more palms you will find our little paradise the perfect spot for a getaway! Cabin 2 offers a comfortable queen size bed as well as a...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulfshore Cottage: 3BR Family-Friendly, Block from Beach1 / 24
    (24)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
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    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2017
    I was lucky enough to secure another stay, my third at this wonderful cottage.Every facility that you would need is available within the cottage . Well stocked for your beach...
    Reviewed 7 November 2017
    This is our third stay at the cottage, and our favorite place to stay when we visit Anna Maria island. It's tough to beat the location, being just a short walk to the beach...
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    About this property
    Your time on Anna Maria Island should be perfectly charming in this classic three-bedroom beach-style cottage perfectly located on the west side of Gulf Drive in the city of Anna Maria. Only steps away from the azure blue waters of the Gulf of Mexico, this unique vacation rental boasts two very...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Enchanted Cottage: 2BR Pet-Friendly Cottage1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, quiet, cozy, Enchanted Cottage is just steps to Tampa Bay and the Historic Anna Maria City Pier, a fun place to fish! A short five blocks to the beautiful powder-soft, white sand and turquoise Gulf water of Anna Maria Island. You may also enjoy the beautiful sunrise from the pier...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Island Place Cottage: 1BR Pet-Friendly Cottage1 / 23
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Cable/satellite TV
    • DVD Player
    • Internet Access
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    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2018
    We decided to go to Ana Maria Island over Christmas 2017 because this was the year we had to share our grown and married children with their in-laws. We had never vacationed...
    Reviewed 29 June 2017
    Great location with shops and restaurants within walking distance. The two piers are also just a short walk away. The cottage is basic but very clean, an ideal base for a few...
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    About this property
    This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
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    • Grill
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk onto the white sands and into the clear waters of the Gulf of Mexico from your beach retreat, the Sunny Daze cottage, one half of a duplex nestled in Holmes Beach on picturesque Anna Maria Island, Florida. Once you arrive at this bright two bedroom/one bath cottage, you can leave your car...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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